#2. Tito Ortiz – former UFC light heavyweight champion

The UFC’s poster-boy when the Fertitta brothers and Dana White brought out the promotion in 2001 was Tito Ortiz. He held the UFC light heavyweight title from 2000 to 2003 and was a wildly popular champion.
Unfortunately, despite once employing White as his manager, Ortiz butted heads on more than one occasion with the UFC’s brass. Most notably, he found himself shelved at the height of his popularity in 2002 after the promotion refused to cave to his financial demands.
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After making five successful defenses of his title, ending with his win over UFC legend Ken Shamrock at UFC 40, Ortiz seemed destined to face top contender Chuck Liddell in his next bout.
However, there was one big problem: Ortiz and Liddell were friends and training partners. While Liddell was willing to commit to the fight, ‘The Huntington Beach Bad Boy’ was not, at least not for the same money he’d been making before.
So, when he couldn’t come to terms with the promotion, they simply pushed him aside and booked a fight between Liddell and Randy Couture for an interim light heavyweight title instead. It was a clear message to ‘The Huntington Beach Bad Boy’, showing him that while he was the UFC’s poster-boy, he could still be replaced at the drop of a hat.
In the end, Ortiz was tempted back into the fold and dropped his title to Couture in their eventual bout at UFC 44. However, while he remained with the UFC until his first retirement in 2012, he continued to butt heads with them over the years, with this incident marking a turning point in his relationship with the promotion and with White.
#1. Randy Couture – former UFC heavyweight and light heavyweight champion

Perhaps the greatest example of a champion ending up at loggerheads with the UFC remains Randy Couture. Sure, ‘The Natural’ stands as one of the promotion’s ultimate legends, as he won the heavyweight title and light heavyweight titles on multiple occasions, but he’s also the only reigning UFC champion to end up facing off with them in court.
Despite Couture once claiming that he felt like he’d been “swimming upstream” with the UFC’s owners for years, his issues only really began in 2007. Prior to that, he felt like one of the darlings of the promotion. Initially winning the UFC heavyweight title in 1997, when his second title reign ended in 2002, he was instantly offered a shot at the interim light heavyweight title against Chuck Liddell.
When his time at 205 pounds ended with his apparent retirement in 2006, the UFC brought him back into the fold a year later by awarding him an instant title shot at heavyweight champ Tim Sylvia. That resulted in Couture becoming a five-time UFC champion.
However, after making his first defense against top contender Gabriel Gonzaga, ‘The Natural’ was angered when the promotion failed to sign former PRIDE champion Fedor Emelianenko and chose to pursue a fight with the Russian elsewhere.
Couture abruptly announced his “resignation” from the UFC, which naturally didn’t sit well with the promotion, who were confident that with ‘The Natural’ under contract, any attempt at fighting for a rival promotion would be illegal. The result was a lengthy legal battle that lasted for the best part of a year, with both sides hitting out at one another in petty fashion in the media. That included a reveal of Couture’s actual pay and contract.
It looked like the issue was heading all the way to court, only for the two sides to abruptly come to terms in late 2008, with Couture returning to the fold to defend his title against Brock Lesnar. In doing so, he earned himself a new, better-paid contract.
However, while ‘The Natural’ seemed to have buried the hatchet with the promotion, things turned sour again in 2013 when he moved to rival promotion Bellator, once again bringing up all the bad feelings and resulting in Dana White stating that he “didn’t respect Couture at all.”